Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000940
Identification
Name: 4-Hydroxy-L-threonine
Description:4-hydroxy-L-threonine is a member of the chemical class known as Alpha Amino Acids and Derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).4-hydroxyl-L-threonine is involved in pyridoxine biosynthesis. This result is consistent with a model in which 4-phospho-hydroxy-L-threonine (synonym, 3-hydroxyhomoserine phosphate), rather than 4-hydroxy-L-threonine, is an obligatory intermediate in pyridoxal 5'-phosphate biosynthesis. (PMID 8595869)
Structure
Thumb
Synonyms:
  • (2S,3S)-2-amino-3,4-dihydroxybutanoate
  • (2S,3S)-2-amino-3,4-dihydroxybutanoic acid
  • 2-Amino-3,4-dihydroxy-(S-(R*,R*))-L-Threonate
  • 2-Amino-3,4-dihydroxy-(S-(R*,R*))-L-Threonic acid
  • 3-Hydroxyhomoserine
  • a-amino-b,g-Dihydroxybutyrate
  • a-amino-b,g-Dihydroxybutyric acid
  • Alpha-Amino-beta,gamma-dihydroxybutyrate
  • Alpha-Amino-beta,gamma-dihydroxybutyric acid
  • Hydroxythreonine
  • α-amino-β,γ-Dihydroxybutyrate
  • α-amino-β,γ-Dihydroxybutyric acid
Chemical Formula: C4H9NO4
Average Molecular Weight: 135.1186
Monoisotopic Molecular Weight: 135.053157781
InChI Key: JBNUARFQOCGDRK-GBXIJSLDSA-N
InChI:InChI=1S/C4H9NO4/c5-3(4(8)9)2(7)1-6/h2-3,6-7H,1,5H2,(H,8,9)/t2-,3+/m1/s1
CAS number: 21768-45-6
IUPAC Name:(2S,3S)-2-amino-3,4-dihydroxybutanoic acid
Traditional IUPAC Name: hydroxythreonine
SMILES:N[C@@H]([C@H](O)CO)C(O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Fatty Acyls
Sub ClassFatty acids and conjugates
Direct Parent Hydroxy fatty acids
Alternative Parents
Substituents
  • Hydroxy fatty acid
  • D-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Alpha-amino acid
  • Short-chain hydroxy acid
  • Beta-hydroxy acid
  • Amino fatty acid
  • Hydroxy acid
  • 1,3-aminoalcohol
  • Secondary alcohol
  • 1,2-diol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Alcohol
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Not Available
Charge:0
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility357.0 mg/mLALOGPS
logP-3.4ALOGPS
logP-4.5ChemAxon
logS0.42ALOGPS
pKa (Strongest Acidic)1.92ChemAxon
pKa (Strongest Basic)8.62ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area103.78 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity28 m3·mol-1ChemAxon
Polarizability12.04 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-4900000000-dbd9d3d88c247a29f9c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9100000000-2070d819d44de1960ae0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9100000000-283552f8bd87ff9d06d5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-8900000000-75b8c2945f1960264b7fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pw9-9400000000-43e8a71f87678ae42e12View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-9000000000-437c14b312f426383b44View in MoNA
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID28330
HMDB IDNot Available
Pubchem Compound ID193577
Kegg IDC06056
ChemSpider ID167988
Wikipedia IDNot Available
BioCyc IDCPD0-2189
EcoCyc IDCPD0-2189
Ligand ExpoTH6